We'll meet you at the dark end of the street.
Obviously, we here at Hooksexup are pretty firmly on the "against" side of infidelity. That said, you'd be a fool to not recognize the rich tradition of the "cheatin' song." Originally established by the Bach cantata "Lyin'-Ass Woman" Citation Needed, the cheatin' song can be pro-cheating, anti-cheating, or somewhere in the middle, as the best ones often are. Here now, then, are the twenty-five best cheatin' songs of all time.
25. Meshell Ndegeocello, "If That's Your Boyfriend (He Wasn't Last Night)"
Meshell Ndegeocello is one of those perennially under-the-radar influencers who've been crushing it for ages. Unapologetically sexy and viciously groovy, "If That's Your Boyfriend" isn't the nicest song on this list, but it's certainly one of the most honest. And man, does it move.
24. The Impressions, "You've Been Cheatin'"
Curtis Mayfield moved on to larger matters (like Hell and social injustice) as his career progressed, but early on, The Impressions were just as concerned with heartbreak as they were with the bigger issues. Mayfield's sky-high voice and the sweet string arrangement behind him put this wonderfully direct ode to infidelity up there with anything coming out of Motown at the time.
23. The Doors, "Back Door Man"
Primal. Relentless. Dark. Much like Jim Morrison himself, "Back Door Man" seems unformed; ancient even. Morrison's unhinged vocal and the band's seductive sturm und drang make this one of the few Doors songs with both feet firmly planted on this plane of perception. Sometimes, infidelity isn't really about subterfuge; sometimes it's more direct than that. And sometimes, it involves eating a whole lot of chicken.
22. Connie Francis, "Lipstick On Your Collar"
A prime early example of the rock n' roll cheatin' song, "Lipstick On Your Collar" is one of the bounciest, most infectious, and squeaky-cleanest odes to infidelity you'll ever hear. But it swings like a beast (that's veteran jazzbo George Barnes's stun-gun guitar solo), and many generations of pop ingenues (like Lana Del Rey) owe their smoky appeal to Francis.
21. Prince, "Head"
Prince has enough "woman done-me-wrong" songs that you'd think he'd be a little more sensitive to infidelity. The poor girl was on her way to be wed, for Chrissakes! But then again, who among us could really resist The Purple One in his prime? And at least he doesn't deflower her totally. That's… kind of nice, right?
20. Tom Waits, "Who Are You?"
Conventional wisdom would go for "Another Man's Vine," from Blood Money, but we prefer "Who Are You" for three reasons. Sure, it's a poetic and elegant expression of the shock of finding out you've been cuckolded and the weary resignation of finding it out again and again. But beyond that, "They're lining up to mad dog your Tilt-A-Whirl / three shots for a dollar, win a real live doll" is one of the best metaphorical accusations of promiscuity ever written.
19. St. Vincent, "Chloe in the Afternoon"
Taking its title from the Éric Rohmer film of the same name, "Chloe in the Afternoon" is a wonderfully skittish portrait of that rarified adulterous meet n' greet: the nooner. "Send you home / Find my heels / Heal my hurt / Grab my choke / Back to work," Annie Clark coos, as the guitars swoon and the bass bumps. It's ecstatic, unsure, and guilty, like the best affairs always are.
18. Donny Hathaway, "Jealous Guy"
Arguing about which version of this song is "best" is pointless. Let's just say that John Lennon wrote a great tune, and that many people have performed it effectively. We just want to give space to a lesser-known, positively incredible reading of a beautiful song, and whether you prefer the original, or the Roxy Music version, you can't argue with the passion Hathaway puts into his rendition. The pathos he puts into the line "I was shivering inside" is indescribable. Put aside the partisanship and call it a win for contrite cheaters everywhere.
17. Michael Jackson, "Girlfriend"
Michael sounds positively gleeful about the position he's putting his lover in in "Girlfriend," which is kind of messed up. We're tempted to call this song a complex analysis of the psychosexual mind games that infidelity engenders against the participants' will, but we can't stop singing it long enough to expand that theory. Also, it has a saxophone break.
16. Carrie Underwood, "Before He Cheats"
One thing modern country definitely has going for it is bombast, and "Before He Cheats" has it in spades. The funny-until-it's-true specificity of the lyrics and that soaring chorus add up to one unfuckable-with ode to a wayward lover and what must have been some thoroughly satisfying auto destruction.
15. Jimi Hendrix, "Hey Joe"
Jimi Hendrix's guitar chops were such that he could take a standard, ageless blues conceit ("Woman has done undesirable thing x / Woman must now die") and turn it into an apocalyptic, existential lament. It's hard to convey heartbreak, dread, rage, and resignation with six strings and a slab of wood, but Hendrix made it look easy.
14. Loretta Lynn, "You Ain't Woman Enough to Take My Man"
We could do an entire list of country cheatin' songs, but we've been forced to cherry-pick the best. Filled with choice put-downs ("Women like you they're a dime a dozen / You can buy 'em anywhere") and steely, vaguely terrifying resolve ("It'll be over my dead body / So get out while you can"), "You Ain't Woman Enough" shows that not every cheatin' song has to be heartbroken and beaten-down.
13. TLC, "Creep"
"Creep" has more conflict to it than its effortless groove suggests. T-Boz knows her man is cheating, but she can't bring herself to leave him, and she doesn't cheat out of revenge, but loneliness. It's a very adult, resigned kind of sadness, and that it won a Grammy and was the second-highest-selling single of 1995 demonstrates that "Creep"'s melancholy resonated with just about everybody who heard it.
12. Destiny's Child, "Say My Name"
One of the best examples of the crazy, wall-of-sound places hip-hop and R&B went in the late '90s/early '00s before everything got all Southern and slowed down. The way the vocal and backing track escalate from a slow boil to full-blown accusation and paranoia is pretty genius. While we can't say we've ever had anyone refer to us as "baby" because they're afraid of confusing us with their lover, we can say that we've danced on a table to this song, which definitely merits its inclusion on this list.
11. Amy Winehouse, "You Know I'm No Good"
Even Amy Winehouse's happiest songs seemed tinged with sadness, so it was no surprise that her heavy songs come across really heavy. In "You Know I'm No Good," she sounds worn out with her own behavior and exhausted by the strain of having to go through the same situations time and time again. The more we found out about her life, the more we learned that she wasn't faking anything.
10. The Beatles, "Run For Your Life"
Even though Lennon disavowed it repeatedly, I happen to love this tune's discordant jingle. The dark lyrics and chord changes over the typically sprightly Beatles rhythms and harmonies is a quirky juxtaposition, even if we found out from some of Lennon's lovers that that line about his temper wasn't an artistic exaggeration.
9. Billy Paul, "Me and Mrs. Jones"
Affairs, particularly the extramarital kind, rarely work out. Nobody leaves their partner, or their kids, and most married affairs just kind of peter out, leaving everybody a little bit sadder and a little bit wiser, hopefully. "Me and Mrs. Jones" recognizes that, nailing a lovelorn ambivalence in a way not a lot of other songs do: "We gotta be extra careful / That we don't build our hopes too high / ' Cause she's got her own obligations and so do I."
8. Patsy Cline, "Your Cheatin' Heart"
Patsy Cline doesn't hold anything back in this performance, but it's a testament to her voice and delivery that the song doesn't come across as hectoring or overly vengeful. Rather, she's coming from a place of deep knowing, regret, and understanding, and that's what makes this song so crushing.
7. Led Zeppelin, "Your Time Is Gonna Come"
Led Zeppelin's entire conceit was fusing the earthy rawness of the blues with otherworldly grandeur. "Your Time Is Gonna Come" is a microcosm of this entire approach: though it's a pretty standard litany of woman-done-me-wrong cliches, the song opens with a church organ and builds to a massed choir of heartbreak. It's one guitar solo away from Valhalla.
6. Bob Dylan, "Most Likely You'll Go Your Way (And I'll Go Mine)"
There's less venom here than there is weariness, and although there's plenty of bluster in some of the recorded versions (the one below is from Before the Flood), the lyrics are more tired than enraged. To wit: "You say ya got some other kinda lover / And yes, I believe you do / You say my kisses are not like his / But this time I’m not gonna tell you why that is." That's a man refusing to rise to the bait, and that's a sentiment the Dylan who wrote "Don't Think Twice" needed some time to grow into.
5. Squeeze, "Tempted"
Squeeze is possibly the most underrated band of all time. And the fact that it took a few commericals to make this song into the hit it never was is lamentable. But lay cosmic injustice aside, and bask in one of the greatest odes to a wandering eye (and possibly wandering loins) ever written. Also, it's got something of a sense of humor to it, which you're no doubt craving by now, having made it this far in this list.
4. Dolly Parton, "Jolene"
In "Jolene," Dolly Parton doesn't have the strength or righteous anger of Loretta Lynn. What's she's got is a heartbreaking laundry list of the reasons her man is straying and one laid-bare plead to just leave him alone. It's a last-ditch move, laced with wheedling praise. It's the action of someone at the end of their rope, and Parton makes us feel every ounce of desperation.
3. Billie Holiday, "I'm A Fool To Want You"
Ray Ellis said that Holiday cried in the control room listening to playback from this song, and it's easy to understand why she might've. Lady in Satin was Holiday's second-to-last album, and she put a lifetime of misfortune and regret into every song. For anyone who's ever beat themselves up over "a love that can't be true / A love that's there for others too," it's hard to listen to this without feeling a little of what she felt in that room.
2. Stevie Wonder, "Part-Time Lover"
"Part-Time Lover" is another tune whose insane catchiness belies its subject matter. Stevie's escalating vocal performance is really what makes "Part-Time Lover" one of the all-time champs of catchy cheatin' tracks. Also noteworthy for a great final-act twist: the cheater becomes the cheatee. "I guess that two can play the game / of part-time lovers / You and me, part-time lovers / But, she and he, part-time lovers."
1. James Carr, "The Dark End of the Street"
Some of the songs on this list are cavalier, some are angry, and a bunch are sad. But none manage to capture the spine-tingling combination of devotion and resignation this song nails. Carr is head over heels for his lover, but fully aware that they have no future. All he can do is keep heading back, hoping against hope for one more night. In some situations, that's all any of us can ask for.
